Category Archives: adventures in dating

Things I have learned about dating in the Real World

College was this weird little bubble where all of my potential boyfriends were pre-selected for me by a group of counselors in the Admissions Office.  My school was so small that before I got involved with anyone I pretty much knew everything about them through the combined powers of mutual friends and Facebook.  I always felt fairly confident that the guys I had my eye on were okay—they weren’t, I assumed, axe murderers in disguise.  But now that I’m in the Real World of Adulthood, there is no pre-screen for my dates other than Google.  The tiny college town where I knew everyone has been replaced by the much-bigger East Coast city where I barely know anyone.  For the past four weeks, I’ve been trying to figure out where exactly one meets men post-grad.  Here are my findings:

At the bank:
The other day as I’m walking to my new bank to complain about some error they have already made, I run into a group of people promoting Sabra Hummus by giving out free containers of their product along with bags of SunChips.  Considering my less-than-affluent status, I gladly take their offerings.  As I continue on to the bank, I run into yet another Sabra cart, and quickly stuff my first round of samples into my bag so I can collect another round.  (Yes, I am that cheap.  Hey, a girl’s gotta eat.)  Long story short, I enter the bank juggling three bags of chips and a stack of hummus containers.  As I’m waiting in the seating area to talk to someone, this dude who’s grungy but not unattractive and is also waiting there strikes up a conversation with me.  He attempts to make a joke about the huge bowl of complimentary lollipops on the table, asks me if I’m still in school (Whyyyyy do I look so young?  I’m in graduate school, man!), and tells me that he is a pianist (Did he just say he’s a penis?  What?  Oh.  I may be in grad school, but I am still immature).  When his banker comes for him, he gets up and goes to shake my hand, which is embarrassingly difficult because first I have to slowly transfer all of my free food to my non-dominant hand.  So much for smoothness.  Unsurprisingly, he does not ask me for my number.

Crossing the street:
As I’m making my way through the crosswalk, this old and I think homeless guy walks right at me, and I have to change course at the last minute to avoid crashing into him.  “Hellllllo” he says in deep voice.  I proceed to run away.

At bars:
Finally, with no success, I begin seeking advice.  “Where do you meet guys?” I ask a friend of mine who has lived in the area for a while, trying desperately not to sound desperate.  “At bars,” she says.  At bars?  I’ve always been kind of wary of that.  I don’t know why—there’s nothing wrong with meeting a guy at a bar.  I guess it’s the part of me that wants to have a really cool story about how I met my guy.  Like, I want to be able to tell people that we did meet randomly at the bank or crossing the street, or because we both reached for the same book at the same time at the bookstore, or because we were both eating alone at a restaurant and decided to share a meal.  I like the idea of meeting someone spontaneously, and somehow meeting a guy at a bar just seems so…expected.  But where, you ask, have I had the best dude turnout?  At bars, of course.  Last Saturday night I accrued two people’s phone numbers and three new Facebook friends, and those individuals were all dudes.  And one of them has been texting me, so it might actually be…promising?  We’ll see.  But you heard it here first: the bar is a den of love.  I especially recommend beer gardens; if your experience is anything like mine, your friend will buy you a huge beer and before you know it you’ll have assembled a clique out of the people you met in the bathroom line.


Bar Mitzvah blues

Before I had gotten my first kiss, I looked up to a friend of mine who was much more experienced than I was.  I would sit for hours, enthralled, while she recounted her boy adventures (yes, that was a Dawson’s Creek reference, thankyouverymuch)—but there was one thing I never understood.  “It just happened,” she’d say, telling me how an innocent hang-out session in a male friend’s basement had become a make-out session.  “It just happened,” when her other friends weren’t looking; “it just happened” between her and the guy she supposedly hated; “it just happened” at school, at the mall, in someone’s car.

I couldn’t fathom, then, how physical encounters progressed from secret desire to reality—and did so naturally, without you having to make a grand declaration or even a small admission of feelings. How could one get from point A (not kissing) to point B (kissing) so smoothly?  It couldn’t be possible!

Of course, I quickly learned the truth of what my friend had said.  Sure, sometimes making moves ends up being pretty awkward, but other times it just happens.  You’re dancing with a dude and then, almost accidentally, his tongue is in your mouth and your friend is giving you a double thumbs-up over his shoulder.  (Um, that happened.)  You’re lying side-by-side on your bed having a nice conversation, but suddenly you’re not talking anymore and things are happening.  Oh, so that’s what she meant.

A few summers ago my family flew across the country for the bar mitzvah of a family friend’s son.  Their much-older son is my age, and at the reception he introduced me to his best friend, who I’ll call Phil.  I didn’t think much of Phil—he seemed like a major bro, and at the time I was trying to avoid guys who appeared too jock-like because I’d had some poor experiences dating athletes in the recent past.  Plus, this was one of those embarrassing occasions when your whole family is around—no time to flirt.

Then—I think because our family friend forced him to out of some bizarre sense of hospitality—Phil invited me and my brother to a party he was hosting at his house that night while his parents were out of town.  Since we had nothing better to do, we agreed to go.  I thought it would be a nice chance to escape the hotel and have a few beers—nothing more.

Flash forward to that night.  We start talking, and Phil doesn’t seem like too much of a bro after all. He majors in Public Health.  And he tells me that he spends his summers volunteering at a clinic in Africa.  He’s the perfect Jewish future-husband of my dreams.  On second thought, I AM IN LOVE WITH HIM.

And then, it just happened.

We were having a conversation, and suddenly he was holding my hand under the table.  (Let’s remember that my younger brother was witnessing this…eeep.  It was definitely a turning point in our siblinghood.)  Then we were kissing in his bedroom.  And yes, he was a good kisser.  Very good.  It was the most fortuitous random hook up of my career—who knew I would meet someone at a bar mitzvah?!

Everyone ended up spending the night (you can imagine the great conversation I had with my brother, who very sweetly and innocently asked, “Where did you sleep last night?”—he had slept in Phil’s sister’s empty room—I assured him that we’d kept it PG-13), which gave me enough time to decide that I really did like Phil, which was unfortunate considering that I was leaving town the next day.  Even my brother agreed that he was a really nice dude.  I felt slightly devastated about the timing of all this, but comforted by the knowledge that I would have good fantasy-fodder for at least another year.  (We could meet again at the next special occasion!)

I won’t pretend that things weren’t awkward at brunch the next morning with the other bar mitzvah guests.  My mother, because she’s my mother, was aware of the situation even without me saying anything.  (When we left she pulled me aside and said, “It was Phil, wasn’t it?”  How does that woman know?)  I hate to say it, but I guess this is one of those stories that just goes to show that you never know where or when you’ll meet someone awesome.  The take home message?  Personally, next time I go to a bar mitzvah, I’ll remember to shave my legs first.

(Un-)sexy librarian

Speaking of asking people out via anonymous note, today I’ll tell the tale of the time that I was on the receiving end of such a solicitation.

Last spring I spent the semester studying in London, but unlike many people who choose to move to a foreign country for half of the year, I was a pretty big geek about my experience.  I specifically selected a program where I could take an intensive, full course load of English classes, and I lived in the library.  Of course I traveled, did a ton of sightseeing, made friends, and drank gallons of tea, too, but my coursework was my main focus for most of the time I was there.  During my exam period, I became particularly fond of a certain spot on one of the upper floors of a library in my neighborhood and spent hours there each day.

I developed a routine: write for a few hours in the morning, take a quick lunch break, write for a few hours in the afternoon, go home for dinner.  It wasn’t very exciting.  Until the day that I returned from my mediocre sandwich, banana, and cup of tea to find a folded piece of paper waiting for me atop my tall stack of books.  I unfolded it.  In the very center of the page written in a blue spidery cursive script was a phone number and the words “Mystery number if you fancy it.”

Hmm.  I immediately narrowed down the possibilities for who the sender could be: the guy who was studying across the room from me or the guy who worked at the library shelving the books.  They were the only other two people who had seen me that day.  I guessed that it was probably the second option: I saw him daily and always scowled at him for playing loud music on his iPod—but maybe he had thought I was staring at him expectantly?  Who knows.  He’d caught my eye because of his wardrobe, which combined formal cardigans and loafers with skinny cuffed pants and bright t-shirts.  He wasn’t my type at all.  So, naturally, I had to give him a chance.  That night, we had a text exchange:

Me: It was nice to get your note today.  I think I know who you are, but I’m not sure.  Do I get a clue?

Him: Sure!  Well, um, er—[yes, he actually wrote this] my hair most needs a comb of everybody on the History floor.  But now that I think of it, I guess anyone could have picked up my note.  Clue please!

Me: I’m the one who always sits crammed in the corner doing more staring into space than actual work.  Does that sound right?

Him: Ha ha, no mistaking you!  [Creepy!]  Well, seeing as this was all just an elaborate preamble to asking you out, do you want to get a drink or something sometime?

Me: That sounds great, but I’m actually going to be traveling for the next week or so.  I can let you know when I get back if that’s okay?

Him: I suppose, but only if you promise to come back with five travelling [the Brits use an extra “l”] stories.  Name is [censored] by the way.  I guess I sort of forgot that that bit comes first…

Me: My name is [censored].  Looking forward to meeting you!

Him: Damn, your name is far cooler than mine.  Laters then!

A few weeks later we made a plan to meet up at this excellent cocktail bar in Covent Garden.  When he invited me I was flattered and excited (uh, he used the words “elaborate preamble” in a text to an English major—I was totally sold), but by the time the actual date rolled around I started feeling nervous.  I didn’t know anything about this guy, who I was meeting in a city I’d only been living in for a few months.  We were meeting in a well-lit, public place.  But still!

That’s when I decided to call in some friends for back-up.  He didn’t know anything about me either, and he definitely didn’t know my friends.  They could show up to the same bar, make sure he didn’t kill me and stuff me in a sack, and provide their opinions on how the date went.  It was a genius-like plan, if I do say so myself.

And it went off flawlessly.  We all got ready together—which cut down on nerves for me—and walked most of the way there together, too.  A few blocks away they turned a corner and I continued on alone.  I saw my mystery man—my friends had dubbed him The Librarian—and we awkwardly introduced ourselves in person and went inside.  We sat down with our drinks and started talking, and about ten minutes later my friends came in.  They played the part of random-people-who-definitely-didn’t-know-me perfectly, sitting a good distance away and taking only discreet glances at us.  They didn’t gesture or make faces, but sat there enjoying their beverages without acting suspicious in the least.

Meanwhile, over at my table, the conversation was dragging.  The Librarian told me that he’d been to Utah before, and I asked if he’d gone skiing.  He hadn’t.  Had I?

“I’m a terrible skier.  I’m very clumsy.”

“Right, yeah, so you’re kind of clumsy?”

“Yeah, I am.”


You get my drift.  After about an hour of zero-chemistry conversation had gone by, he asked if I wanted to leave and check out a different bar in Soho.  I made an excuse about needing to stop by a friend’s house, and we exited the bar together.

“I’m heading this way,” he said, pointing North.  “Which way are you going?”

“That way,” I said, pointing in the opposite direction.

He gave me a quick kiss on the cheek and said that he’d see me soon, back at the library.  We parted, I walked around the corner, counted very slowly to ten, and walked right back into the bar to join my friends.  We began debriefing immediately.

“I could barely see what he looked like underneath all that hair!” said one of my friends.  True, he did have a curly mop and a rather unattractive mustache.

“Yeah, and I could tell from your body language that you weren’t into him,” said the other.

After an unsuccessful evening, the only thing left to do was buy another round and then go bar hopping.  And just like that, a lackluster date turned into an awesome girls night.  If only every encounter could end that way!

Asking out the waiter

I realized early in my college career that if I wanted to go on dates, I was going to have to do the asking myself.  I don’t subscribe to that whole thing about the guy having to make the first move.  It always feels good when a dude expresses interest in me, so why shouldn’t I express my interest in a dude and (potentially) make him feel good?  Also—let’s be real here—I wasn’t getting asked out by too many people, so this was a decision made mostly of necessity.

And it worked!  Ask and you shall receive, apparently.  At least three-fourths of the dates I’ve gone on over the course of this academic year were initiated by yours truly.  Some were awful, some were bearable, and others rocked.  More often than not, people would tell me that they were glad I had asked.

Of course, it’s an imperfect science.  A few months ago when I was out to brunch with a friend for her birthday, I asked out the cute guy who was serving us.  I recognized him from other times I’d eaten there—this town has like three restaurants—and he joked around with me throughout the meal.

“Don’t let me forget my umbrella,” I said to my friend as we sat down.

“The first rap I ever wrote was about an umbrella!” he interrupted, singing a few lines from it.  He was quirky—I liked that.

“So, was that rap just a one time thing or the start of a career?” I asked when he came to refill the water.

“Oh, just the beginning of a very successful career.  I’m kind of a big deal.”

“Can I buy your album?”

“You probably won’t be able to afford it—it’s quite a commodity.”

And on and on.  “I should leave my number on the bill,” I said to my friend, not seriously considering the idea.  She urged me to do it.  Impulsively, I did.  I wrote a note with my digits that said: “To the cute waiter with the blue hat: So that I can say I knew you before your album went platinum.”  Then we bolted from the restaurant.

I wondered if he’d find it beneath the stack of bills, if he’d accidentally throw it out, if he’d know it was from me, if he wasn’t into women, if he had a girlfriend—and in the midst of all this worrying, he texted me.

“Hey!  This is [censored] the server from [censored].  Sneaky little message you left on the table!  Well, now that you have my number we should grab coffee sometime.  Thanks for the fun note!”

We went back and forth for a while, and I learned that he had graduated from my school the year before and now lived in the nearest big city.  He told me that he might be back in town that weekend, and promised to let me know if he did indeed come.  I was excited that he wanted to see me again and that my random ask-out had worked.  A quick Facebook stalking session (everyone does it!) confirmed that he was as good-looking as I’d thought earlier in the day, and he was a stellar banter partner to boot.  Score.

You guessed it, though—he never got in touch.  Not that weekend, not the week following, and not the week after that.  I’ve seen him around campus a few times since, but he doesn’t seem to recognize me.  (Okay, okay, I have hidden from him every time.  I might be brave enough to ask dudes out, but I still chicken out sometimes!)  I thought it would be weird to remind him about our potential date, so I just let things fizzle…or rather, disappear.

Oh well.  You can’t blame a girl for trying.

Remember, remember the, um, 19th of May

Just a friendly reminder about (drumroll, please): The First Ever Installment of Dude, Where’s My Boyfriend Guest Posters!  Send me a story of (a) dating adventure(s) that you’ve had!  Whatever you’ve got, send it along—this is going to be fun!

  • Keep your tales appropriate (who knows who could stumble across this blog on the internetz?).
  • Try to be respectful in your language (which you would be anyway, right?).
  • Please refrain from including revealing details about your conquests, as I like to keep things on here as friendly as can be.
  • I will keep you as anonymous as you choose—please specify how you’d like me to introduce you.

The deadline is Saturday, May 19th.  That’s one week, people!

You should also include some words.

Digital Get Down (yes, the title of this post is the name of an ‘NSYNC song)

I have a new obsession: Twitter.

I’ve only had an account for two weeks, but I’m totally hooked.  (Follow me! @dudewheresmyBF.)  I get to post my random thoughts about anything and everything, and 15 other people read them! (Yes, only 15 as of yet.  Have I mentioned that you should follow me?)  I get to read others’ random thoughts about anything and everything!  I can read the random thoughts of my favorite celebrities, too: Rachel Dratch, the contestants from the past few seasons of The Bachelor/Bachelorette, and A.J. McLean from the Backstreet Boys!  I am in love.

I guess I’ve always had an interest in putting my writing out there in online forums.  It began with Xanga when I was in middle school, then MySpace in early high school, later LiveJournal, now WordPress.  This is the first time, though, that I’ve shared intimate details of my personal life—and the personal lives of people I’m involved with—in such a public way.  It feels kind of weird sometimes.

And it also brings up the questions—those many a dating blogger has tackled—of if and how and when to tell those people I’m involved with that I do this.  Luckily—well, unluckily for my dating life, but luckily in terms of this particular conundrum—I haven’t faced this problem with anyone yet.  But still—sometimes I feel kind of bad for writing about people as they remain blissfully unaware.  I keep thinking of that line in the Destiny’s Child song “Survivor” when the narrator (?? do they have that in songs?  I am such an English major) is saying that even though this dude has treated her like shit she’s not going to stoop to his level: “I’m not gonna diss you on the internet—cuz my mama taught me better than that.”  I am trying really hard not to diss anyone on the internet!  I am trying not to reveal identifying details or say anything horribly mean and judgmental. I’m trying to do right by the guys I’m writing about, even if I don’t think they did right by me.

It’s risky business, my friends.  Here’s a cool New York Times article I read the other day that talks all about it (Twitter specifically).  Some couples found the solution to be asking each other for permission before posting anything questionable.  I’m not sure how that would work; and I feel kind of defensive: this is my blog, containing my feelings, so why should I have to operate based on what someone else thinks?  On the other hand, when I finally meet someone I really, really care about, of course I wouldn’t want to do anything that could conceivably offend, embarrass, or hurt them.  But I also worry about the day when I have to tell someone I’m dating that I write this blog. How will that conversation go?  All of the potential bad reactions are kind of scary to think about.

I don’t know what the answer is here.  What do you guys think?

A timeline of timing

They say that timing is eveything, and over the past few years I have found this cliché adage to be, well, true.  The more I date, the more I’m convinced that whether or not someone is “ready” for a relationship is the key to things working out or totally tanking.  As a case in point, I give you:

The Dude Where’s My Boyfriend Timeline of Timing (Abridged Version*)

Let’s go back to the spring of 2009, the second semester of my freshman year of college.  Enter Dumb Jock (the stereotype is, in this case, very, very legitimate), who I (dumbly) fell for—hard.  He treated me terribly, ignoring me for weeks at a time and then wanting to hook up again, but for some reason I couldn’t stay away.  When we finally ended things (i.e. when he started ignoring me completely), I was crushed.  For a year.  It’s almost laughable to me now—I’ve gained enough distance from the whole situation to be able to lovingly call that period the “Dark Days” of my dating life—but at the time I felt completely lost and hurt.  For several weeks I went to bed crying and woke up still crying.  It took me months to feel vaguely okay, and even longer than that to feel remotely secure enough to really put my heart into another relationship.  Obviously, the guy hadn’t been right for me, but he had been someone who I’d experienced a lot of “firsts” with, and I felt the loss keenly.

I was still in my recovery phase during fall 2009, when I hooked up with a guy who was clearly looking for more with me.  I thought that I was open to exploring that with him, but the experience of being with someone while continuing to mourn someone else was bewildering, and I quickly called it off.  In the spring, I was finally ready to move on from Dumb Jock, and so began another weird hybrid of a hook up/relationship with a different Dumb Jock, who was only slightly better than the first.  (What was I thinking?  It remains a mystery even to me.)  I went through another rough period after splitting up with Dumb Jock 2—in much the same, silent way that I’d split up with Dumb jock 1—but I came back to school in the fall of 2010 feeling fed up with dating losers and ready—for real!—to graduate to an adult relationship.

Over that summer I’d been keeping in touch with a guy from my school, and things seemed promising.  We hung out platonically a few times at the beginning of the semester, and one night when he came to my room we started fooling around.  He was pretty shy and even though we were lying on my bed cuddling it didn’t seem like he was going to do anything, so I kissed him.  (Not an easy thing to do for someone who had been wounded in the recent past—I was proud of myself.) He kissed me back, but only barely—and a few days later showed up to my room again, in daylight, to tell me that he wasn’t ready for anything.

Fast forward through the spring, summer, and fall, when no one of major interest shows up and I remain ready as ever.  And then, in the winter of 2011, I meet a guy who I’m 100% sure is My Next Big Love, and things go swimmingly for a week or so, I prepare to take his last name and wonder how many kids he’ll want to have, and BAM—you guessed it, folks: he’s not ready.  And then I’m not ready, because I’m 100% sure that I’ll never love again, and my heart feels like it has shriveled up and withered away.  And then I’m ready again, because I realize that that guy kind of really blew, and that I deserve better.  I’m ready now, but being ready, I’ve found, often means that you need to wait.  For a long time.

Not to get too scientific about it, but sometimes the conditions are right for love.  You’re both in the right place in your lives, you both want the same things, there’s chemistry between you and also intellectual attraction, your families like each other.  But there are so many things that go into making a relationship work, it’s such a hard balance to strike.  If one tiny part of the equation is off, the whole thing could go under.

But then sometimes the stars align.  You’re ready and he’s ready.  It never ceases to amaze me.

*Abridged because I’m only hitting the highlights here.  If I detailed all of my college mistakes, this would likely turn into more of a pity party than the mere hang-out session I intend it to be.

I wanna write with you (all niiiight)

If you read this blog regularly or even at all you’ll know that there’s a little thing lurking on my horizon called college graduation.  In a few weeks my time will be totally taken over with receptions, ceremonies, and awkward family meet-and-greets.  I won’t have much time to post, and so I give you (drumroll, please): The First Ever Installment of Dude, Where’s My Boyfriend Guest Posters!  This is very exciting, really.

According to the “About” section of this blog, herein lie the “true confessions of a single lady looking for the right guy in all the wrong places.”  I WANT YOU to write to me with the stor(y)(ies) of your own dating adventure(s).  Then, I will feature them here.  We’ll laugh, we’ll cry, we’ll go home single.

There are basically no restrictions here, except that I politely ask you to keep your tales appropriate (who knows who could stumble across this blog on the internetz?) and try to be respectful in your language (which you would be anyway, right?).  Also, please refrain from including revealing details about your conquests, as I like to keep things on here as friendly as can be.  I will keep you as anonymous as you choose—please specify how you’d like me to introduce you.

Although I identify as a straight female, that doesn’t mean that you do—people who identify in all ways are encouraged to send me something.

The deadline is Saturday, May 19th.  Write to me!

This weird picture wants you to be a DWMBF guest poster! You know you want to…


An addendum to my last post

Yesterday I wrote that my current dating philosophy can be summed up by Kelly Clarkson’s song “I Do Not Hook Up,” and as soon as I posted I started thinking about what that actually means.  Everyone and his or her mother has a personal definition of “hooking up” (though I don’t really want to know what your mother’s is).  While some people define hooking up as sex, others, like me, define it as a little harmless making out, probably some nudity, and maybe a night spent (sleeping! or pretending to) at the other person’s place.  So when I say that “I Do Not Hook Up” is a song I identify with at the moment, don’t worry—I’m not implying that I’ve taken a vow of abstinence or anything (no hate to anyone who has, of course).

What I am implying is that I’m in the market for something more than your typical meet-at-a-party-he’s-kinda-cute-oh-well-why-not tryst.  As you probably already know from the name of this blog, I’m in the market for a boyfriend.  I’m sick of hooking up with random dudes who I have no feelings for just for the hell of it.  I hate how I always end up developing feelings for said random dudes anyway, and how those feelings are never reciprocated.  I want something steady and long-term; I want someone who I can introduce to my parents—someone who they’ll actually like, too.

But—like everything related to dating, apparently—it’s hard.  I keep thinking about my favorite cheesy movie, Keeping the Faith, the scene where the Anna (Jenna Elfman) and Brian (Edward Norton) are in Central Park and she asks him how he stays celibate as a priest (seriously, watch it).  “There comes a point,” she tells him, “when I just crave contact.  You know?  Like I wanna touch someone and be touched.”  Not the most eloquent of lines, sure, but I think she’s onto something.  There are so many things I love about being single—not least the roominess of an unshared bed—but it also becomes incredibly frustrating very quickly.  As much as I want to hold out for the right guy, to make my hook ups meaningful instead of mediocre, the waiting is not fun in the slightest.

Okay, maybe that’s an exaggeration—dating is, or at least can be, fun, and playing the field certainly has its benefits.  You get to know yourself and what you’re looking for really damn well, for one thing.  But there inevitably comes that point when I find myself, like Anna, just craving contact with another person.  And what to do when that mood strikes?  Over the past few years my theory has generally been to go with it, but more recently it’s gotten old.  I’ve realized that as great as the hook ups can be, hooking up in general is not something I find satisfying.  So I’ve resolved not to do it before getting to know the person.

Sometimes I falter, but other times resisting the urge can lead to something a little closer to what I’m looking for.  A few months ago, for example, I was leaving a bar with a guy I’d been flirting with all night.  He put his arm around me and started walking me home, but before we got there I stopped and said point-blank: “I don’t think we should hook up right now, but I do think you’re really cool and that we should hang out sometime in the daylight.”  He was totally okay with this, gave me his number, and we did hang out—the next day I asked him to coffee.  He didn’t end up being quite as cool as I’d thought, but at least I knew that before anything went down.

Rock on, Kelly Clarkson.


My prevailing feeling after my date this week is that DATING. IS. SO. AWKWARD.  Moreover, I. AM. SO. AWKWARD.  Seriously—while I am generally confident in my intelligence (at least when it comes to literature and every single episode of Dawson’s Creek; my father once had to send me talking points about current events when I had a date with a Politics major), meager humor, and ability to carry on a conversation, I am not so sure that I would want to date me.

To be fair to all parties involved, I would not say that the date was a failure.  He scored a point by bravely asking me out in a public place where a lot of other people could hear my potential acceptance/rejection.  I scored a point by getting back on the horse, so to speak, and putting myself back out in the scary, weird, and often creepy world of dating.  We both scored points by coming up with enough stuff to say to each other for an hour and a half.

My problem on dates—and let’s face it, in life in general—is not being able to get out of my own head long enough to just experience my feelings.  Instead, I feel compelled to analyze my emotions and level of attraction throughout the entire thing, such that I spend the whole time engaged in an inner monologue that goes something like this:

Me: Hmm, do I think the face he makes when he laughs is cute?

Me: Yeah, I guess it’s kind of nice.

Me: Wait, nevermind, not that nice.  Yep, I’m definitely not attracted to him at all.

Me: Well, that’s kind of an exaggeration.  I guess he is sort of good looking…

Me: But would I want to take off his clothes?

Me: Sure.  Maybe not.  I DON’T KNOW.

[end scene]

You get the picture.  It is nearly impossible for me to stay in the moment of the actual date rather than planning out what I’m going to report to my friends after the fact.  As a result, I feel kind of stiff when I’m talking to someone, and I think it makes me come off as stressed out, which is no fun for a) me or b) my date.  This time, for example, I was so wrapped up in coming up with interesting questions to ask this guy to keep our chat rolling along smoothly—and he seemed to be doing the same—that it became more of a mutual job interview than a date.  Eeep.

The only good news is that my mental babble often provides a good shorthand for how much I like someone.  Usually, if I don’t find myself questioning how I feel—or if the answers to my mental checklist of Do I find him attractive?  Am I going to say yes if he asks me out again? etc. are all an unequivocal “YES”—then I know that this person is someone I dig.

Unfortunately, it’s a fallible method.  I’ve had awful first dates followed by amazing second dates and amazing first dates followed by awful second dates.  It’s always great when the chemistry is just there, but I’m a firm believer that it can also take some time to grow in.  The question is, how much time?  How long do you wait for the dates to stop feeling awkward and start being awesome?

Comment with answers, if you’ve got ’em!